HCID 178418689, compound → HCID 178468157, compound

HRID 1852809Notes

Reaction equation

HRID 1852809 reaction equation
[CH3:1][Mg+].[Br-].CON(C)[C:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH3:15])[CH2:11][CH2:10]1)=[O:8]>C1COCC1>[CH3:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:7](=[O:8])[CH3:1])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 178418689HCID 178418689, compoundHCID 178502717HCID 178502717, compound

Product 1

HCID 178468157HCID 178468157, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (352 mL, 1.1 mol, 3 mol/L) was added dropwise slowly to a stirred solution of trans-N-methoxy-N,4-dimethylcyclohexanecarboxamide (130 g, 0.7 mol) in THF (1.2 L) at 0° C. The mixture was stirred at room temperature for 2 hours. TLC showed no starting material (petroleum ether/ethyl acetate=5:1) left. The mixture was cooled to 0-5° C., and quenched by the addition of saturated NH4Cl (0.1 L) and H2O (2 L). The mixture was extracted with ethyl acetate twice. The combined organic layer was washed with brine and dried over Na2SO4, filtered and concentrated under reduced pressure to give crude 1-(trans-4-methylcyclohexyl)ethanone, which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 2.27-2.19 (m, 1H), 2.10 (s, 3H), 1.90 (d, J=12.8 Hz, 2H), 1.70 (d, J=12.8 Hz, 2H), 1.35-1.23 (m, 3H), 0.96-0.85 (m, 5H).

Workup

  1. waitleft
  2. temperatureThe mixture was cooled to 0-5° C.
  3. customquenched by the addition of saturated NH4Cl (0.1 L) and H2O (2 L)
  4. extractionThe mixture was extracted with ethyl acetate twice
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b650f2f1a01a406fb47f2a7f4c33ac9c
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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